Synthesis
In an argon-filled glove box, potassium tert-butoxide (5.6 mg, 0.05 mmol), manganese catalyst (0.005 mmol), tetrahydrofuran (0.5 mL), and 1,8-naphthidine (0.25 mmol) were added sequentially to a 4 mL glass bottle equipped with a stir bar. The bottle was capped, and a needle with a 3 cm long vent hole (1 mm in diameter) was inserted into the cap. The glass bottle was then placed in an autoclave. After removing the autoclave from the glove box, the argon gas in the autoclave was replaced with hydrogen (3 × 10 bar), and then 80 bar of hydrogen was introduced. The reaction was carried out at 120 °C for 16 h. After the reaction was completed, the mixture was cooled in an ice-water bath, and the gas inside the autoclave was carefully released. The resulting reaction product system was sampled for GC quantification and column chromatography separation to obtain the target product.
Application
1,2,3,4-Tetrahydro-1,8-naphthidine is an organic intermediate that can be obtained by reducing 1,8-naphthidine with hydrogen. 1,2,3,4-Tetrahydro-1,8-naphthidine can be used to prepare (E)-3-(5,6,7,8-tetrahydro-1,8-naphthidine-3-yl)acrylic acid. This class of compounds is a FabI inhibitor with antibacterial activity and therefore can be used to treat bacterial infections in mammals, especially humans.
